journal article·2023-03

Anticancer drug doxorubicin (DOX) loading performance of functionalized polyaniline (PANI) surface with active carbon

Musa Mutlu Can, Shalima Shawuti, Ferdane Danisman Kalindemirtas, Gokce Erdemir, Durdane Serap Kuruca, Satoru Kaneko, Zerrin Aktas, Oral Oncul

Journal of Materials Science· Volume 58· Issue 11
Publisher page

Abstract

The study was based on surface functionalization of conductive PANI (polyaniline) polymer for drug delivery systems. Specifically, an electrochemical polymerization technique was performed for the synthesis of PANI layers on tin-doped indium oxide (In2O3:Sn or ITO)-coated PET (polyethylene terephthalate) substrates. Three main factors were studied: binding ability, drug-loading ability and drug-delivering ability. PANI layers, combined with active carbon (AC), were organized as biomaterials to carry the anticancer drug doxorubicin (DOX). Two different films, PANI and PANI with AC, were polymerized in the emeraldine salt form of PANI. A comparison of the two samples proved that AC molecules enabled DOX molecules to bind to the PANI surface, as observed by the UV-Vis absorption spectra of the films. DOX molecules were detected by UV-Vis spectra with an absorption peak at 547 nm. Findings from drug loading/release tests and in vitro cytotoxicity results confirm that these films can be used as drug delivery systems. This work underlines essential role of AC in the PANI layer for drug delivery.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Conducting polymers and applications · Electrochemical sensors and biosensors · Analytical Chemistry and Sensors

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (75)

Show source-provided references
1. Wang Y, Zhu C, Pfattner R, Yan H, Jin L, Chen S, Molina-Lopez F, Lissel F, Liu J, Rabiah NI, Chen Z, Chung JW, Linder C, Toney MF, Murmann B, Bao Z (2017) A highly stretchable, transparent, and conductive polymer. Sci Adv 3:e160207610.1126/sciadv.1602076 ↗
2. Kuhn HH, Child AD, Kimbrell WC (1995) Toward real applications of conductive polymers. Synth Met 71:2139–214210.1016/0379-6779(94)03198-F ↗
3. Balint R, Cassidy NJ, Cartmell SH (2014) Conductive polymers: towards a smart biomaterial for tissue engineering. Acta Biomater 10:2341–235310.1016/j.actbio.2014.02.015 ↗
4. Sun Q, Qian B, Uto K, Chen J, Liu X, Minari T (2018) Functional biomaterials towards flexible electronics and sensors. Biosens Bioelectron 119:237–25110.1016/j.bios.2018.08.018 ↗
5. Guo B, Ma PX (2018) Conducting polymers for tissue engineering. Biomacromolecules 19:1764–178210.1021/acs.biomac.8b00276 ↗
6. Kaur G, Adhikari R, Cass P, Bown M, Gunatillake P (2015) Electrically conductive polymers and composites for biomedical applications. RSC Adv 5:37553–3756710.1039/C5RA01851J ↗
7. Wang C, Cheng L, Liu Z (2011) Drug delivery with upconversion nanoparticles for multi-functional targeted cancer cell imaging and therapy. Biomaterials 32:1110–112010.1016/j.biomaterials.2010.09.069 ↗
8. Wolinsky JB, Colson YL, Grinstaff MW (2012) Local drug delivery strategies for cancer treatment: gels, nanoparticles, polymeric films, rods, and wafers. J Control Release 159:14–2610.1016/j.jconrel.2011.11.031 ↗
9. Le TH, Kim Y, Yoon H (2017) Electrical and electrochemical properties of conducting polymers. Polymers Basel 9:15010.3390/polym9040150 ↗
10. Alizadeh N, Shamaeli E (2014) Electrochemically controlled release of anticancer drug methotrexate using nanostructured polypyrrole modified with cetylpyridinium: release kinetics investigation. Electrochim Acta 130:488–49610.1016/j.electacta.2014.03.055 ↗
11. Karim MR, Lee CJ, Lee MS (2007) Synthesis and characterization of conducting polyaniline-activated carbon nanocomposites. J Appl Polym Sci 103:1973–197710.1002/app.24968 ↗
12. Dhand C, Dwivedi N, Mishra S, Solanki P, Mayandi V, Beuerman RW, Ramakrishna S, Lakshminarayanan R, Malhotra B (2015) Polyaniline-based biosensors. Nanobiosensors Dis Diagn 201:25–46
13. Qazi TH, Rai R, Boccaccini AR (2014) Tissue engineering of electrically responsive tissues using polyaniline based polymers: a review. Biomaterials 35(33):9068–908610.1016/j.biomaterials.2014.07.020 ↗
14. Arteshi Y, Aghanejad A, Davaran S, Omidi Y (2018) Biocompatible and electroconductive polyaniline-based biomaterials for electrical stimulation. Eur Polymer J 108:150–17010.1016/j.eurpolymj.2018.08.036 ↗
15. Thanh LC, Nga DTN, Lam NVB, Chung PD, Nhi LTT, Sinh LH, Thu VT, Lam TD (2021) Acetylcholinesterase sensor based on PANi/rGOfilm electrochemically grown on screen-printed electrodes. Vietnam J Chem 59(2):253–26210.1002/vjch.202000158 ↗
16. Patil JP, Mahajan HS (2015) A review on polymer drug conjugate—what, why and how? IJPSR 6(11):4611–4621
17. Monkman AP, Stevens GC, Bloor D (1991) X-ray photoelectron spectroscopic investigations of the chain structure and doping mechanisms in polyaniline. J Phys D Appl Phys 24:7310.1088/0022-3727/24/5/017 ↗
18. Focke WW, Wnek GE, Wei Y (1987) Influence of oxidation state, pH, and counterion on the conductivity of polyaniline. Am Chem Soc 91:5813–5818
19. Albuquerque JE, Mattoso LHC, Balogh DT, Faria RM, Masters JG, MacDiarmid AG (2000) A simple method to estimate the oxidation state of polyanilines. Synth Met 113:19–2210.1016/S0379-6779(99)00299-4 ↗
20. Wojciechowski PM, Zierkiewicz W, Michalska D (2003) Electronic structures, vibrational spectra, and revised assignment of aniline and its radical cation: theoretical study. J Chem Phys 118(24):1090010.1063/1.1574788 ↗
21. Vilar G, Tulla-Puche J, Albericio F (2012) Polymers and drug delivery systems. Curr Drug Deliv 9(4):367–39410.2174/156720112801323053 ↗
22. Paolino D, Sinha P, Fresta M, Ferrari M (2006) Drug delivery systems. In: Webster JG (ed) Encyclopedia of medical devices and instrumentation. John Wiley & Sons Inc, Hoboken, pp 437–495
23. Kost J, Langer R (2012) Responsive polymeric delivery systems. Adv Drug Deliv Rev 46(1–3):125–148
24. Ege D, Kamali AR, Boccaccini AR (2017) Graphene oxide/polymer-based biomaterials. Adv Eng Mater 19:170062710.1002/adem.201700627 ↗
25. Yan X, Chen J, Yang J, Xue Q, Miele P (2010) Fabrication of free-standing, electrochemically active, and biocompatible graphene oxide-polyaniline and graphene-polyaniline hybrid papers. ACS Appl Mater Interfaces 2(9):2521–252910.1021/am100293r ↗
26. Thompson BC, Murray E, Wallace GG (2015) Graphite oxide to graphene. Biomater Bionics Adv Mater 27(46):7563–7582
27. Tian H-C, Liu J-Q, Wei D-X, Kang X-Y, Zhang C, Du J-C, Yang B, Chen X, Zhu H-Y, Nuli Y-N, Yang C-S (2014) Graphene oxide doped conducting polymer nanocomposite film for electrode-tissue interface. Biomaterials 35:2120–212910.1016/j.biomaterials.2013.11.058 ↗
28. Ahadian S, Huyer LD, Estili M, Yee B, Smith N, Xu Z, Sun Y, Radisic M (2017) Moldable elastomeric polyester-carbon nanotube scaffolds for cardiac tissue engineering. Acta Biomater 52:81–9110.1016/j.actbio.2016.12.009 ↗
29. Zengin H, Kalaycı G (2010) Synthesis and characterization of polyaniline/activated carbon composites and preparation of conductive films. Mater Chem Phys 120(1):46–5310.1016/j.matchemphys.2009.10.019 ↗
30. Ioannidou O, Zabaniotou A (2007) Agricultural residues as precursors for activated carbon production—a review. Renew Sustain Energy Rev 11(9):1966–200510.1016/j.rser.2006.03.013 ↗
31. Miriyala N, Ouyang D, Perrie Y, Lowry D, Kirby DJ (2017) Activated carbon as a carrier for amorphous drug delivery: effect of drug characteristics and carrier wettability. Eur J Pharm Biopharm 115:197–20510.1016/j.ejpb.2017.03.002 ↗
32. Butowska K, Woziwodzka A, Borowik A, Piosik J (2021) Polymeric nanocarriers: a transformation in doxorubicin therapies. Materials 14:213510.3390/ma14092135 ↗
33. Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C (1969) Adriamycin, 14-hydroxydaimomycin, a new antitumor antibiotic from S. Peucetius var. caesius. Biotechnol. Bioeng 11:1101–111010.1002/bit.260110607 ↗
34. Ravina E (2011) Drugs from microbiological sources. The evolution of drug discovery: from traditional medicines to modern drugs, 1st edn. Wiley-VCH, Weinheim, p 296
35. Montaseria H, Sayyafana MS, Tajerzadeh H (2005) Preparation and characterization of poly-(methyl ethyl cyanoacrylate) particles containing 5-aminosalicylic acid. Iran J Pharm Res 1:21–27
36. El-Kady AM, Kamel NA, Elnashar MM, Farag MM (2021) Production of bioactive glass/chitosan scaffolds by freeze-gelation for optimized vancomycin delivery: effectiveness of glass presence on controlling the drug release kinetics. J Drug Deliv Sci Technol 66:10277910.1016/j.jddst.2021.102779 ↗
37. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65(1–2):55–6310.1016/0022-1759(83)90303-4 ↗
38. Mahla DK, Bhandari S, Rahaman M, Khastgir D (2013) Morphology and cyclic voltammetry analysis of in situ polymerized polyaniline/graphene composites. J Electrochem Sci Eng 3(4):157–166
39. Fernández J, Bonastre J, Molina J, del Río AI, Cases F (2017) Study on the specific capacitance of an activated carbon cloth modified with reduced graphene oxide and polyaniline by cyclic voltammetry. Eur Polymer J 92:194–20310.1016/j.eurpolymj.2017.04.044 ↗
40. Wang Q, Li J-L, Gao F, Li W-S, Wu K-Z, Wang X-D (2008) Activated carbon coated with polyaniline as an electrode material in supercapacitors. New Carbon Mater 23(3):275–28010.1016/S1872-5805(08)60030-X ↗
41. Fomo G, Waryo TT, Baker P, Iwuoha EI (2016) Electrochemical deposition and properties of polyaniline films on carbon and precious metal surfaces in perchloric acid/ acetonitrile. Int J Electrochem Sci 11:10347–1036110.20964/2016.12.102 ↗
42. Aggadi SE, Loudiyi N, Chadil A, Zoubida EA, Hourch AE (2020) Electropolymerization of aniline monomer and effects of synthesis conditions on the characteristics of synthesized polyaniline thin films. Mediterr J Chem 10(2):138–14510.13171/mjc102020021114sea ↗
43. Hussain AMP, Kumar A (2003) Electrochemical synthesis and characterization of chloride doped polyaniline. Bull Mater Sci 26(3):329–33410.1007/BF02707455 ↗
44. Korent A, Soderžnik KŽ, Šturm S, Rožman KŽ (2020) A correlative study of polyaniline electropolymerization and its electrochromic behavior. J Electrochem Soc 167:10650410.1149/1945-7111/ab9929 ↗
45. Rohom AB, Londhe PU, Mahapatra SK, Kulkarni SK, Chaure NB (2014) Electropolymerization of polyaniline thin films. High Perform Polym 26(6):641–64610.1177/0954008314538081 ↗
46. Kulkarni AK, Schulz Kirk H, Lim TS, Khan M (1999) Dependence of the sheet resistance of indium-tin-oxide thin films on grain size and grain orientation determined from X-ray diffraction techniques. Thin Solid Films 345(2):273–27710.1016/S0040-6090(98)01430-8 ↗
47. Devi PS, Chatterjee M, Ganguli D (2002) Indium tin oxide nano-particles through an emulsion technique. Mater Lett 55(4):205–21010.1016/S0167-577X(01)00647-4 ↗
48. Abdiryim T, Xiao-Gang Z, Jamal R (2005) Comparative studies of solid-state synthesized polyaniline doped with inorganic acids. Mater Chem Phys 90(2–3):367–37210.1016/j.matchemphys.2004.10.036 ↗
49. Pouget JP, Jozefowicz ME, Epstein AJ, Tang X, MacDiarmid AG (1991) X-ray structure of polyaniline. Macromolecules 24(3):779–78910.1021/ma00003a022 ↗
50. Rossier JS, Bercier P, Schwarz A, Loridant S, Girault HH (1999) Topography, crystallinity and wettability of photoablated PET surfaces. Langmuir 15(15):5173–517810.1021/la9809877 ↗
51. Trchova M, Moravkova Z, Blaha M, Stejskal J (2014) Raman spectroscopy of polyaniline and oligoaniline thin films. Electrochim Acta 122:28–3810.1016/j.electacta.2013.10.133 ↗
52. Radoičić MB, Milošević MV, Miličević DS, Suljovrujić EH, Ćirić-Marjanović GN, Radetić MM, Šaponjić ZV (2015) Influence of TiO2 nanoparticles on formation mechanism of PANI/TiO2 nanocomposite coating on PET fabric and its structural and electrical properties. Surf Coat Technol 278:38–4710.1016/j.surfcoat.2015.07.070 ↗
53. Bláha M, Zedník J, Vohlídal J (2015) Self-doping of polyaniline prepared with the FeCl3/H2O2 system and the origin of the Raman band of emeraldine salt at around 1375cm-1. Polym Int 64:1801–180710.1002/pi.4983 ↗
54. Lindfors T, Ivaska A (2005) Raman based pH measurements with polyaniline. J Electroanal Chem 580:320–32910.1016/j.jelechem.2005.03.042 ↗
55. Cho S, Lee JS, Jun J, Kim SG, Jang J (2014) Fabrication of water-dispersible and highly conductive PSS-doped PANI/graphene nanocomposites using a high-molecular weight PSS dopant and their application in H2S detection. Nanoscale 6:15181–1519510.1039/C4NR04413D ↗
56. Bai S, Zhao YÜ, Sun J, Tian Y, Luo R, Li D, Chen A (2015) Ultrasensitive room temperature NH3 sensor based on a graphene–polyaniline hybrid loaded on PET thin film. Chem Commun 51:752410.1039/C5CC01241D ↗
57. Liu X-X, Zhang L, Li Y-B, Bian L-J, Su Z, Zhang L-J (2005) Electropolymerization of aniline in aqueous solutions at pH 2 to 12. J Mater Sci 40(17):4511–451510.1007/s10853-005-0854-x ↗
58. Olszówka M, Russo R, Mancini G, Cappelli C (2016) A computational approach to the resonance Raman spectrum of doxorubicin in aqueous solution. Theor Chem Acc 135:2710.1007/s00214-015-1781-9 ↗
59. Depan D, Shah J, Misra RDK (2011) Controlled release of drug from folate-decorated and graphene mediated drug delivery system: synthesis, loading efficiency, and drug release response. Mater Sci Eng, C 31:1305–131210.1016/j.msec.2011.04.010 ↗
60. Rana S, Gallo A, Srivastava RS, Misra RDK (2007) On the suitability of nanocrystalline ferrites as a magnetic carrier fordrug delivery: functionalization, conjugation and drug release kinetics. Acta Biomater 3:233–24210.1016/j.actbio.2006.10.006 ↗
61. Elbialy NS, Fathy MM, Khalil WM (2015) Doxorubicin loaded magnetic gold nanoparticles for invivo targeted drug delivery. Int J Pharm 490(1–2):190–19910.1016/j.ijpharm.2015.05.032 ↗
62. Dong Z, Gong H, Gao M, Zhu W, Sun X, Feng L, Fu T, Li Y, Liu Z (2016) Polydopamine nanoparticles as a versatile molecular loading platform to enable imaging-guided cancer combination therapy. Theranostics 6(7):1031–104210.7150/thno.14431 ↗
63. Silva EF, Machado ES, Vasconcelos IB, Junior SA, Dutra JL, Freire RO, Costa NB (2020) Are the absorption spectra of doxorubicin properly described by considering different tautomers? J Chem Inf Model 60:513–52110.1021/acs.jcim.9b00785 ↗
64. Mirza AZ, Shamshad H (2011) Preparation and characterization of doxorubicin functionalized gold nanoparticles. Eur J Med Chem 46(5):1857–186010.1016/j.ejmech.2011.02.048 ↗
65. Huang X, Brazel CS (2001) On the importance and mechanisms of burst release in matrix-controlled drug delivery systems. J Control Release 73(2–3):121–13610.1016/S0168-3659(01)00248-6 ↗
66. Wang L, Chang MW, Ahmad Z, Zheng H, Li JS (2017) Mass and controlled fabrication of aligned PVP fibers for matrix type antibiotic drug delivery systems. Chem Eng J 307:661–66910.1016/j.cej.2016.08.135 ↗
67. Huang X, Brazel CS (2001) On the importance and mechanisms of burst release in matrix-controlled drug delivery systems. J Control Release 73:121–13610.1016/S0168-3659(01)00248-6 ↗
68. Sawyer AJ, Piepmeier JM, Saltzman WM (2006) New methods for direct delivery of chemotherapy for treating brain tumors. Yale J Biol Med 79:141–152
69. Sedghi R, Shaabani A, Mohammadi Z, Samadi FY, Isaei E (2017) Biocompatible electrospinning chitosan nanofibers: a novel delivery system with superior local cancer therapy. Carbohyd Polym 159:1–1010.1016/j.carbpol.2016.12.011 ↗
70. Dong Y, Chin SF, Blanco E, Bey EA, Kabbani W, Xie XJ, Bornmann WG, Boothman DA, Gao J (2009) Intratumoral delivery of β-lapachone via polymer implants for prostate cancer therapy. Clin Cancer Res 15(1):131–13910.1158/1078-0432.CCR-08-1691 ↗
71. Ahnfelt E, Sjogren E, Hansson P, Lennernas H (2016) Pharmaceutics, drug delivery and pharmaceutical technology in vitro release mechanisms of doxorubicin from a clinical bead drug-delivery system. J Pharm Sci 105:3387–339810.1016/j.xphs.2016.08.011 ↗
72. Zhuang WR, Wang Y, Cui PF, Xing L, Lee J, Kim D, Jiang HL, Oh YK (2019) Applications of π-π stacking interactions in the design of drug-delivery systems. J Control Release 294(28):311–32610.1016/j.jconrel.2018.12.014 ↗
73. He A, Lei B, Cheng C, Li S, Ma L, Suna S, Zhao C (2013) Toward safe, efficient and multifunctional 3D blood-contact adsorbents engineered by biopolymers/graphene oxide gel. RSC Adv 3:2212010.1039/c3ra44775h ↗
74. Montaseri H, Sayafan MS, Tajerzadeh H (2005) Preparation and characterization of poly-(methyl ethyl cyanoacrylate) particles containing 5-aminosalicylic acid. Iran J Pharm Res 4(1):21–27
75. Sawy AM, Barhoum A, Gaber SAA, El-Hallouty SM, Shousha WG, Maarouf AA, Khalil ASG (2021) Insights of doxorubicin loaded graphene quantum dots: synthesis, DFT drug interactions, and cytotoxicity. Mater Sci Eng C 122:11192110.1016/j.msec.2021.111921 ↗